Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 18, Problem 18.41P
You have learned two ways to make an alkyl benzene: Friedel–Crafts alkylation, and Friedel–Crafts acylation followed by reduction. Although some alkyl benzenes can be prepared by both methods, it is often true that only one method can be used to prepare a given alkyl benzene. Which method(s) can be used to prepare each of the following compounds from benzene? Show the steps that would be used.
a. b. c. d.
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Show how you would synthesize each compound from benzene, toluene, or phenol using the following reactions:
Reactions
1. Halogenation
2. Nitration
3. Sulfonation
4. Friedel-Crafts acylation
5. Friedel-Crafts alkylation
6. Oxidation of methyl group
7. Reduction of nitro group
• Choose the starting material from the drop-down list
• Enter the number(s) of the desired reactions in the order that you wish to use them without commas between
• If a reaction is used more than once, enter its number each time you wish to use it
Compound 1: 5-chloro-2-methylbenzenesulfonic acid
Starting material: toluene
Reaction(s): 31
Compound 2: m-bromobenzoic acid
Starting material: [benzene
Reaction(s):
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benzene, toluene, phenol
Drug name: p-cresol
Chapter 18 Solutions
Organic Chemistry-Package(Custom)
Ch. 18 - Prob. 18.1PCh. 18 - Prob. 18.2PCh. 18 - Prob. 18.3PCh. 18 - Prob. 18.4PCh. 18 - Prob. 18.5PCh. 18 - What acid chloride would be needed to prepare each...Ch. 18 - Prob. 18.7PCh. 18 - Draw a stepwise mechanism for the following...Ch. 18 - Prob. 18.9PCh. 18 - Prob. 18.10P
Ch. 18 - Prob. 18.11PCh. 18 - Prob. 18.12PCh. 18 - Problem 18.14 Draw all resonance structures for...Ch. 18 - Classify each substituent as electron donating or...Ch. 18 - Prob. 18.15PCh. 18 - Label each compound as more or less reactive than...Ch. 18 - Rank the following compounds in order of...Ch. 18 - Problem 18.18 Rank the following compounds in...Ch. 18 - Prob. 18.19PCh. 18 - Problem 18.20 Draw the products of each...Ch. 18 - Prob. 18.21PCh. 18 - Prob. 18.22PCh. 18 - Devise a synthesis of each compound from the...Ch. 18 - Problem 18.24 Draw the products of each...Ch. 18 - Problem 18.25 Draw a stepwise mechanism for the...Ch. 18 - Problem 18.26 Draw the products of each...Ch. 18 - Prob. 18.27PCh. 18 - Prob. 18.28PCh. 18 - Problem 18.29 How could you use ethylbenzene to...Ch. 18 - Prob. 18.30PCh. 18 - Problem 18.31 What steps are needed to convert...Ch. 18 - Problem 18.32 Synthesize each compound from...Ch. 18 - Synthesize each compound from benzene.Ch. 18 - Prob. 18.34PCh. 18 - 18.35 What is the major product formed by an...Ch. 18 - Draw the products formed when phenol (C6H5OH) is...Ch. 18 - Prob. 18.37PCh. 18 - Draw the products of each reaction. a. e. i. b. f....Ch. 18 - What products are formed when benzene is treated...Ch. 18 - Draw the products of each reaction. a.d. b.e. c.f.Ch. 18 - You have learned two ways to make an alkyl...Ch. 18 - Prob. 18.42PCh. 18 - Prob. 18.43PCh. 18 - 18.45 Explain why each of the following reactions...Ch. 18 - Prob. 18.45PCh. 18 - 18.47 For each of the following substituted...Ch. 18 - Which benzene ring in each compound is more...Ch. 18 - 18.49 For each N-substituted benzene, predict...Ch. 18 - Explain each statement in detail using resonance...Ch. 18 - Prob. 18.50PCh. 18 - Explain why the meta product is formed in the...Ch. 18 - 18.53 Rank the aryl halides in each group in order...Ch. 18 - Prob. 18.53PCh. 18 - 18.54 Draw a stepwise mechanism for the following...Ch. 18 - Prob. 18.55PCh. 18 - 18.56 Draw a stepwise, detailed mechanism for the...Ch. 18 - Prob. 18.57PCh. 18 - 18.58 Draw a stepwise mechanism for the following...Ch. 18 - Draw a stepwise mechanism for the following...Ch. 18 - Prob. 18.60PCh. 18 - Draw a stepwise mechanism for the following...Ch. 18 - Prob. 18.62PCh. 18 - Prob. 18.63PCh. 18 - Synthesize each compound from benzene and any...Ch. 18 - Synthesize each compound from benzene and any...Ch. 18 - Synthesize each compound from toluene (C6H5CH3)...Ch. 18 - Prob. 18.67PCh. 18 - Use the reactions in this chapter along with those...Ch. 18 - Prob. 18.69PCh. 18 - Prob. 18.70PCh. 18 - Problem 18.69 Identify the structures of isomers A...Ch. 18 - Prob. 18.72PCh. 18 - Problem 18.71 Compound X (molecular formula ) was...Ch. 18 - Prob. 18.74PCh. 18 - The NMR spectrum of phenol () shows three...Ch. 18 - Explain the reactivity and orientation effects...Ch. 18 - Prob. 18.77PCh. 18 - Prob. 18.78PCh. 18 - Prob. 18.79PCh. 18 - Prob. 18.80P
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